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Web Video / ContraPoints

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Hi girls, it's Ms. Points again!

Condoms and orgies and mass immigration,
malt liquor 40s and miscegenation,
boys who use dildos and girls with cock rings
these are my favorite degenerate things

Absinthe and coffee and bitchy sarcasm
estrogen, crying, and fruitless orgasms
antifa furries and NB drag kings
these are my favorite degenerate things

Natalie Wynn is an ex-academic philosopher and leftist YouTuber who makes videos about social justice issues like gender, race, sexuality, anti-fascism, anti-capitalism, and feminism on her channel ContraPoints.

Natalie's videos are known for their combination of dark humor, colorful lighting, flamboyant costumes and makeup, and mind screwy, Lynch-like atmosphere. What started as an attempt to deliver information on social issues eventually grew to incorporate many cartoonish characters and plot lines, high production values and extreme lighting.

The other strong theme of her videos is her gradual coming out as a transgender woman. In early videos, Natalie identified as a crossdressing man, before coming out as genderqueer (nonbinary), and then finally as a transgender woman. To watch her videos is to watch a woman coming to terms with her own gender identity.


She also began her channel (by her own admission) as something of a political centrist, gradually moving further and further to the left due to the events of 2016 – the ascendancy of Trump and the growth of the alt-right. Her channel has since criticised centrist liberals for, she claims, providing indirect support to the far-right by lumping fascists and anti-fascists together, and by taking white supremacists' excuses about just wanting "free speech" at face value.

As of early 2020, she has removed her old, pre-transition videos (up to "Decrypting The Alt-Right"). She's explained that watching her old content is very painful for her as it triggers intense dysphoria, and those videos being available on the internet for everyone to see eventually became too much for her to feel comfortable with.


Compare with her friend and fellow YouTuber H.Bomberguy, who also uses humor and theatricality to talk about similar issues. Contrast with Shaun, another (if less aesthetically pleasing) leftist with a very dry sense of humor, and Philosophy Tube, a fellow leftist philosopher and occasional voice-over in her videos.

Not to be confused with another YouTube channel called Counter Arguments, which discusses rhetorics and logical fallacies in general.

Some tropes you'll find in her videos include:

  • Accidental Misnaming:
    • Jackie Jackson accidentally calls Abigail "Annabel" in The Aesthetic.
    • Is Casual Sex Bad for your Soul? is a video response to The Distributionist, but because of his icon note , she accidentally calls him Chesterton. She decides to just run with it for the entire video.
  • The Alcoholic: This trope is basically part of Contra's "aesthetic".
  • All Jews Are Ashkenazi: Saul gets this treatment. Fritz even sings "Hava Nagila" at him while he looks on incredulously.
  • Ambiguous Gender Identity: Several of her characters look at gender identities and what that means. When she started transitioning, so did her non-female characters. This is explicitly pointed out with Lady Foppington and Fritz (now Freya) note .
  • Armour-Piercing Question: At the end of TERFs. "Dost Thou Bleed?" Albeit because it confuses Tiffany more than anything.
  • Arson, Murder, and Jaywalking:
    • In Jordan Peterson, Natalie disgustedly calls philosopher David Hume "a fuckin' racist, and also Scottish."
    • In Why I Quit Academia, the video has a content warning that it contains "alcoholism, eating disorders, vomit, tedious introspection."
    • The Are Traps Gay? video has yet another one warning that it contains "discussion of transphobic slurs and violence, and graphic displays of anime."
  • The Bad Guy Wins:
    • In Debating the Alt Right, the Nazi Fritz completely upstages Saul in their interview with Jackie.
    • Discussed in The Left, as Contra criticizes the left's lack of presentability, explaining that it's the right wing's tactic to make their fascist beliefs more popular among the public.
  • Berserk Button: There is no better way to get on Natalie's bad side than helping Nazis reach larger audiences.
  • Bittersweet Ending: Autogynephilia ends with final words from Natalie in which she explains that making this video was extremely humiliating, difficult and personal, she shared things in this video that she "wouldn't even tell her own diary on her deathbed", for the scrutiny of people who despise her. She says that the only hope she has in life is that one day she'll be loved by someone who sees her as a woman. Otherwise, she's fucked. She concludes the video with the phrase "This has been a tough one, girls. I dare say you've earned a song." She then plays a truly heartwarming cover of "Three Times a Lady" by Lionel Richie, before transitioning into Rocky Horror's "Time Warp".
  • Blunt "Yes": In the Jordan Peterson video, when Abigail Cockbane asks Natalie if longer nails is the only thing womanhood means for her. Natalie only nods in answer.
  • Body Motifs: She notes how the far right tend to use skulls as a symbol of natural hierarchy, from 20th century race scientists using phrenology to justify white supremacy to modern incels ranking male attractiveness based entirely on bone structure.
  • Both Sides Have a Point: Not always the case, but many of Natalie's videos feature rhetorical debates with no clear winner. One prominent example is the episode Punching Natzees, where two characters discuss whether punching Nazis can ever be justified.
  • Brains and Bondage: Her video Violence features her discussing different philosophies surrounding violence while being repeatedly disciplined. By herself.
  • By "No", I Mean "Yes": Gender Critical starts out this way.
    Natalie: First of all, a reminder that this episode is a female-only space, so if there are any men here today... Get Out!
    Natalie: ...I mean, unless you enjoy watching the very interesting things that women do on our own. In which case, like! Comment! Subscribe!
  • Call-Back: Transtrenders is one to The Aesthetic. It opens with Tiffany Tumbles debating a sympathetic NB character (in the same way Abigail Cockbane was debating Tabby), and she goes on to have a conversation with the same character Tabby did (who's this time defending NB people and other trans people who're labelled "transtrenders" by some). The whole episode hits many of the same beats (albeit contrasting Tiffany and Tabby's reactions to them) and is likely meant to demonstrate how Wynn's views have changed since the episode.
  • The Cameo:
    • Natalie's videos often involve cameos from other left-wing YouTubers including Lindsay Ellis, H.Bomberguy, Shaun, The 1 Janitor, Steve Shives, Dick Coughlan and Claudia Brown.
    • A common joke among the Fandom is that Shaunnote  has a cameo in What Is Race.
  • Casanova Wannabe: Examined in Pick Up Artists. It starts out comical and soon gets pretty depressing.
  • Cast Full of Gay:
    • Many of Natalie's characters are trans or otherwise gender non-conforming people, even if they are neo-Nazis.
    • The original idea behind Fritz was that of a Camp Gay crossdressing Nazi - a paradox in and of itself.
    • Tabby and Adria are two trans women in a polyamorous relationship.
  • Casting Gag:
    • Abigail Cockbane, a radical feminist who accuses trans women of being men in wigs, is herself being played by a trans woman in a wig.
    • In The Aesthetic, Tracy Mounts, a drag queen that Natalie plays, comments on how some people say she's a man dressed as a lady, but she's actually a lady who used to be a man dressed as a man dressed as a lady.
      Tracy: Explain that, Professor Butler.
  • Catchphrase:
    • Natalie saying "As a trans woman..." in an obnoxious snotty tone before delivering her perspective on an issue through that lens.
    • "Let's watch an instructional video to learn more." This is used by various characters to segue into a portion of the current video's essay, introduced on the old TV that's frequently used.
    • Debuting characters tend to introduce themselves to the audience with "It is I, [insert name here]!"
    • “Hey, how are you?”
  • Celebrity Paradox: In The Aesthetic, Justine refers to (and shows footage of) a 2017 debate between Blaire White and "that YouTuber with the pink wig", i.e. ContraPoints herself.
  • Chivalrous Pervert: Part of the Contrapoints aesthetic. She's been playing with the Depraved Homosexual / Depraved Bisexual trope while discussing feminist and LGBT issues since the beginning of her channel.
  • Classical Music: Natalie has said she's always liked classical music. She uses it plenty in her videos.
  • Corpsing: It's extremely rare for Natalie to leave any of this in the final edit, but Gender Critical left two instances of it in.
  • Costume Porn: As time has gone on the costumers have become more numerous and extravagant. Compare Foppington in What is Race? with her later appearance in Jordan Peterson.
  • Covert Pervert:
    • Abigail Cockbane. In Is BDSM Feminist? she argues that she just doesn't see what's supposed to be so appealing about bondage, before going on a whole spiel explaining her erotic fantasies of being spanked by a dominant master and having wax dripped over her naked boobs.
    • In Autogynephilia, she holds a riding crop in her hand, which Natalie asks about. She quickly and angrily defends herself by saying it's for horseback riding.
  • Crossdresser: Natalie used to crossdress in her twenties.
  • Despair Event Horizon: How she summarizes the "Black Pill" of the incel community, when an incel develops a world view that sexual value is genetic. Because they come to believe that they don't meet the qualifications for attraction from women, they are doomed to a life without romantic love or sex, and so they should just "lie down and rot". This mindset is what leads to suicidal ideation and, in extreme cases like with Elliot Rodger, mass murder.
  • Did Not Get the Girl: Justine admits to her frienemy Tiffany that she is in love with her in Transtrenders, prompting Tiffany to leave and get drunk without reciprocating.
  • Downer Ending: The Aesthetic is a socratic dialectic (meaning a dialogue between two fictional characters representing two different points of view) on gender performativism. There is no coda, no clear "right or wrong" as is usual for these kind of videos, but this particular video has somewhat of a mean spirit to it. It cuts to the core of many, many trans people's anxieties and fears. Justine literally spells out, "I guess we can't win, can we?" Even though Justine tells Tabby that she doesn't want to fight with her, and that as long as they both exist as trans women in this world, they'll always be sisters, the tone remains somber.
  • Dude Looks Like a Lady / Lady Looks Like a Dude: Played with, to both comedic and serious effect.
  • Early Installment Weirdness: Her earlier videos lack the Mood Lighting that has since become her trademark. Since she had yet to come to see herself as a transgender woman, those videos also see her sporting a deeper voice and occasionally more masculine clothing. Most of them feature her exclusively as herself, with her bevy of characters not yet appearing. Her humor style was also drier and more blunt.
  • Erotic Eating: For example, stuffing your mouth with corn dogs as a metaphor for dick ("The West"), or sensually licking out mussels as a metaphor for eating pussy ("Pick-Up Artists"), or subverted when she beats the crap out of a zucchini.
  • Faux Affably Evil: Freya, the campy trans Nazi. She can appear as more open-minded, calm and rational than her liberal opponents, but it's clear she only tries to legitimize Nazi views in the eyes of the audience.
  • Framing Device:
    • Lampshaded in Is BDSM Feminist? with Contra just making up a name for the host on the spot. "Whatever, it- it doesn't matter." After all, the talk-show format is only the framing device for the dialectic.
    • Pointed out in Punching Natsees - Bruce asks Trixie how her week has been, as is normal in a Skype call between friends, and she argues that it doesn't matter, this is just a framing device, he should just get to the point.
  • Friendly Enemy: In Transtrenders, it it shown that the conservative trans-woman Tiffany and progressive trans-woman Justine, who despised each other in Tiffany Tumbles, are now friends, albeit friends who still constantly debate about trans issues.
  • Go-Karting with Bowser: Has had some surprisingly civil debates/meetings with Shoe0nHead, Sargon Of Akkad and others.
  • Godwin's Law: Even has a "Batman"-inspired cartoon sound effect. However, since several videos look at fascism and alt-right arguments, Godwining will happen from time to time.
  • Golden Mean Fallacy: Jackie Jackson is particularly fond of pulling this off. Natalie herself is very suspicious of this trope, seeing it as giving legitimacy to the alt-right.
  • Grey and Gray Morality: Tabby and Justine in The Left and The Aesthetic. Trixie and Bruce in Punching Natsees.
  • Have I Mentioned I Am Heterosexual Today?: Shame is largely about compulsory heterosexuality, or the behavior that a gay woman puts on out of denial of her sexual orientation, and Natalie's experiences with it.
  • The Hedonist: Studied in Pick Up Artists and Is Casual Sex Bad for your Soul? and played up in Degeneracy.
  • Hitler Ate Sugar: Defied in the Jordan Peterson video. In spite of similarities between Peterson's concept of postmodern neo-Marxism and the Cultural Marxism theory spread by neo-Nazis (itself based on the "Cultural Bolshevism" idea of the original Nazis), Natalie refuses to make comparisons between Peterson and fascists, and instead she tries to dissect and criticize the concept itself.
  • Horrible Judge of Character: Jackie Jackson falls for all of Fritz's lies no matter how blatant they are, as do many centrists with neo-nazis.
  • The Horseshoe Effect: Deconstructed in Punching Natsees as the debate breaks down into an argument, as Internet debates are wont to do. Unlike most versions of this trope, the argument is between a far left anarchist and a centre left liberal.
  • Hypocritical Humor: In Cultural Appropriation, Natalie, a white woman, criticizes cultural appropriation while wearing Mexican Day of the Dead face paint.
  • Instructional Film: In Gender Dysphoria, the Doctor shows Natalie one about "xenomorphic gender parasitosis", a fictional disease that's a stand-in for transsexuality. The film consists of clips of Natalie in a wig and a nice dress eating strawberries and whipped cream with jazz music in the background - interrupted by disturbing war footage with fear-mongering text about this fictional illness and mechanical booming playing over it.
  • "It" Is Dehumanizing : In Gender Critical, she points out that being called "female" is better than being called "it."
  • Jidai Geki: Transtrenders uses a conversation and musical composition evocative of this genre for debate between Tiffany Tumbles and Baltimore Maryland, though no combat actually happens.
  • Kangaroo Court: In Autogynephilia, Contra gets put on trial for being an autogynephile. The judge is Michael Bailey (an author and supporter of the transphobic autogynephilia theory), the accuser is the gender critical subreddit, represented by Abigail Cockbane. You can guess the verdict.
    Abigail: Your honor, the defendant does not bleed - I find that pretty conclusive.
  • Killed Off for Real: In The Left, viewers find out that Bruce and Trixie from Punching Natsees killed each other in their gun fight.
  • Knight of Cerebus: The videos featuring Freya are generally much darker than Natalie's other videos. Granted Sie is a Nazi.
  • Lady Drunk: Jackie Jackson in particular gets drunker and drunker as the conversation spirals into insults and arguing instead of constructive discussions (with herself!).
  • Lost in Transmission: At the end of Does the Left Hate Free Speech part 2 and The West.
  • Love Across Battlelines: Played for laughs. She makes jokes about how RooshV and Armoured Skeptic are attractive men while being deeply critical of their policies and principles. Her being in love with The Golden One has turned into a Running Gag. Probably the most explicit joke is the bath scene in Jordan Peterson, though. On the topic of Peterson, she also refers to him multiple times as her "daddy dom". As Clifton Mark of The Atlantic explained in an article about the show, this is a core part of Natalie's approach to dealing with her opposition:
    This is not to say that Wynn is Socrates’s second coming, simply that she shares Socrates’s view that philosophy is more an erotic art than a martial one. As she puts it, she’s not trying to destroy the people she addresses, but seduce them.
  • Madness Mantra:
    • "I feel fine".
    • "Emotional damage" in Is Casual Sex Bad for your Soul?
    • Tiffany Tumble's "I'm in control".
  • Men Are Tough: Mocked in Alpha Males. Then it takes a Mood Whiplash as she realizes The Golden One is a downright Nazi...
  • Metaphorgotten: The watermelon metaphors in The Apocalypse are a parody of scientific analogies that never work on the intended audience anyway, and as such are already off-track by the second sentence.
    Imagine the year is 2100. I want you to picture the earth as a vagina and imagine you're a gynecologist and you're using a speculum to examine the inside of a watermelon. How does that make you feel, kids? I bet you wish your irresponsible gas-guzzling parents had done something to stop this!
  • Mood-Swinger: Peter Coffin's voice over work in Autogynephilia takes it the extreme, where he fluctuates between a highly sexual tone and a cold monotone, often within the same sentence.
  • Mood Whiplash: Alpha Males video starts as a light-hearted Testosterone Poisoning video. Then the Golden One starts to talk about the Jewish Question...
    • That said; It still retains a light tone throughout.
  • Non-Nude Bathing: All bath scenes since Natalie has come out as a trans woman. Even Abigail wears a slip in the tub as part of her "moon ritual".
  • No Periods, Period: Parodied in TERFs. And how.
  • Not So Different: Discussed in Incels, in which she notes that despite apparently being on diametrically opposed sides of the political and cultural spectrum, large segments of Incel culture share uncomfortable similarities with several of the pre-transition trans groups she used to frequent. In particular, both are rather insular communities with their own specialized language populated by those who feel shunned and excluded by a hostile world. However, despite supposedly being spaces to bring lonely, vulnerable and insecure people together for help, support and defense against abuse from outsiders, both end up becoming self-reinforcing echo chambers for the most toxic, harmful and self-loathing impulses of their members.
  • Rape Is a Special Kind of Evil: Deconstructed in Western Rape Cultures. She also points out that while Western culture demonizes rape and rapists, consent is a more complicated problem.
  • Repetitive Audio Glitch: It happens during her laugh in the beginning of Does the Left Hate Free Speech? (Part 1) for some reason.
  • Retraux: Contra uses a lot of 80's aesthetic, from the neon lights to VHS film filters.
  • Right-Wing Militia Fanatic: Parodied with Fritz/Freya.
  • Running Gag:
    • Whenever the words "as a trans woman" is used as a qualifier for Natalie's point of view, it's always said in the same incredibly high-pitch, nasally voice.
    • Natalie throwing milk on herself in a bathtub.
    • Natalie's weird crush on The Golden One.
    • Variations on the phrase "speaking as a biological woman..." said in full Sarcasm Mode. Similarity, when her identity as a trans woman comes up (generally once a video), she winds up about how it's "super hard" and she's "opening up" about something that she "never talks about on her channel," but... She's actually a trans woman.
  • Sanity Slippage: Frequently. The biggest example is in Psychiatry.
  • Satire: The first part of What is Wrong With Capitalism, part 2 is a clear jab at Jordan Peterson, particularly his use of overly sophisticated language to obfuscate his meaning. Although this applies to many academic philosophers.
  • Screw Yourself: There are a few jokes about Natalie lusting after her her pre-transition self, such as admiring some old Shirtless Scenes and referring to her past self as "a real yum-yum". If you count the various characters she plays, then there are plenty of them that actually engage in this, such as near the end of "Pick Up Artists" (where she gets it on with the personification of 'Love').
  • Self-Deprecation: Prone to making fun of herself and describing herself as "trash". It's mostly played for laughs, but on occasion becomes quite serious, as she actually had endured serious struggles with depression and gender dysphoria in the past.
  • Shout-Out: Here and there, for example to Falco ("Clock me, Amadeus!") in Jordan Peterson, or "Try the wine!" from A Clockwork Orange as a Running Gag.
  • Smart People Play Chess: Justine and Tabby play chess in The Left.
  • Soapbox Sadie: Played with, as each character presents an argument, but each argument is also flawed. ''TERFs'' features "Abigail Cockbane, Radical Feminist."
  • Sophisticated as Hell: Natalie positively revels in this trope. She will often address the audience in a highly articulate and formal manner, using sophisticated words and phrases, but then casually throw in profanity or informal neologisms without batting an eyelid.
  • Strawman Political: Subverted and critiqued. She's good at presenting multiple points of view, although she's clear where her political compass points. Tabby as the straw Antifa communist is a good example of this.
  • Surprisingly Good Foreign Language: If she's not at least conversational in German, she's pretty good at faking it, especially when Freya speaks. Overlaps with Gratuitous German in some cases, such as saying "Teil Eins" and "Teil Zwei" and so forth for "Part One," "Part Two," etc.
  • Take a Third Option: When Natalie describes her inability to identify with any gender in an early video ("Non-Binary Genders"), she says that rather feeling like a man or a woman she feels like shit.
  • Those Wacky Nazis: Freya is a fascist and the rise of fascism is discussed in ''Decrypting the Alt-Right: How to Recognize a F@scist.''
  • Trans Equals Gay:
    • Debated on "The Freedom Report" in the episode Tiffany Tumbles.
    • Deconstructed in the Are Traps Gay? video.
  • Transgender Fetishization: The trope is discussed in the Autogynephilia video, in which she points to J. Michael Bailey's The Man Who Would Be Queen as popularizing the trope for modern audiences. In the book Bailey and his assistants refer to trans women as unnaturally attractive (to the point of Uncanny Valley), and with a natural affinity toward sex work.
  • Trans Tribulations: A recurring theme in her videos.
  • Unexpectedly Dark Video: Gender Dysphoria is a very personal short film about gender dysphoria and coming to terms with being trans. It was essentially Natalie's coming out on her YouTube channel, and it explicitly addresses the feeling that she's disgusting, deeply uncomfortable with her body, nobody understands or accepts her for being trans and that she fears she will never be loved. These issues are addressed in Tiffany Tumbles and The Aesthetic as well, although there more in the form of Mood Whiplash and Downer Ending.
  • Unnecessary Makeover:
    • invoked Played for Laughs in The Left. In this case, the Marx Engels Reader gets a neon pink cover to appeal to the youths.
    • Pointed out by Tabby in The Aesthetic, as Justine is telling her she needs to present more femininely and try harder to pass, and thus forces Tabby into a role she's not comfortable with.
  • White Male Lead: Mentioned in passing in How I became a Feminist SJW.
  • Worthy Opponent: Natalie believes that the Golden One is a genuinely funny and adorable guy who just unfortunately happened to get involved into various neo-Nazi stuff. Curiously, the Golden One himself has some nice things to say about Natalie as well.


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